Is making the first move a good idea? (as a girl)

I'm not really used to sharing details about myself online whatsoever but I don't really feel comfortable talking to my friends about this because they all share the same opinions and I want a fresh perspective before I make any decisions. 

I have a close friend that I've known since I was maybe 7 years old. We've both admitted to each other that over the course of our friendship we've had crushes on each other just not at the same time. Which feels so frustrating. We're not as close anymore but recently, and completely randomly too, he's kind of just popped into my head and won't leave. 

He used to often send really cringy tiktok's about couples and make indirect comments about how he really wants a relationship. Although whenever we are at the same parties we don't really speak, but as soon as I leave he decides it's the perfect time to begin a conversation. And he used to come up to my friends after I had left and ask them where I went etc. He's told his friends before (multiple times) about how he's had feelings. He got jealous and a little angry at me when I told him another guy asked me out on a date, but I can't tell whether I'm reading into it too much.

We don't go to the same school anymore so that makes me feel more inclined to just be honest about how I feel since I don't think there'd be any serious consequences if nothing happens. Especially since I'm planning on moving abroad next year. Not even in a year, less than that, like 10 months.

He's really nice and extremely funny. I don't expect him to feel the same or even for anything to happen but I just want the satisfaction of knowing that I was honest. And because then I'll never wonder what if. He got his heart broken but that was over a year ago so I don't think it affects him anymore, but then again I'm not 100% sure.

Let me know what you think :))